WO2023084343A1 - Procédé de fabrication d'un composé aromatique monocyclique - Google Patents

Procédé de fabrication d'un composé aromatique monocyclique Download PDF

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Publication number
WO2023084343A1
WO2023084343A1 PCT/IB2022/060127 IB2022060127W WO2023084343A1 WO 2023084343 A1 WO2023084343 A1 WO 2023084343A1 IB 2022060127 W IB2022060127 W IB 2022060127W WO 2023084343 A1 WO2023084343 A1 WO 2023084343A1
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Prior art keywords
catalyst
reactor
monocyclic aromatic
oxygen
aromatic compound
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PCT/IB2022/060127
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English (en)
Inventor
Brant Lane AGGUS
Daniel Travis Shay
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Koch Technology Solutions, Llc
Koch Technology Solutions UK Limited
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Publication of WO2023084343A1 publication Critical patent/WO2023084343A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/02—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon from oxides of a carbon
    • C07C1/12—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon from oxides of a carbon from carbon dioxide with hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
    • C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11

Definitions

  • the present disclosure relates to a process for the high- selectivity conversion of oxygen-containing organic molecules to monocyclic aromatic compounds, such as benzene, toluene or xylene, or mixtures thereof.
  • Monocyclic aromatic compounds such as BTX (mixtures of benzene, toluene, and xylene isomers), are important chemicals in the petroleum refining, petrochemical, and specialty chemical industries.
  • BTX and related C9/C10 aromatic compounds can be formed from oxygen-containing organic molecules, such as alcohols.
  • US8962902B2 and US9388092B2 describe processes for converting alcohols to BTX compounds in the presence of zeolite catalysts at elevated temperatures. However, these high temperatures can result in detrimental effects to the zeolite catalyst. For example, coke may be formed and deposited on the catalyst surface and pores, effectively blocking active sites on the catalyst and reducing activity.
  • a process for manufacturing at least one monocyclic aromatic compound comprising contacting an aluminosilicate catalyst with an oxygen-containing organic molecule in a reactor to produce the monocyclic aromatic compound and in situ-generated hydrogen gas; and introducing CO2 into the reactor and allowing the CO2 to react with the in situ-generated hydrogen gas to form additional monocyclic aromatic compound.
  • At least a portion of the CO2 and in situ-generated hydrogen gas may react to form carbon monoxide.
  • the process may further comprise allowing the carbon monoxide to contact the catalyst.
  • a process for manufacturing at least one monocyclic aromatic compound comprising contacting an aluminosilicate catalyst with an oxygen-containing organic molecule in a reactor to produce the monocyclic aromatic compound and in situ-generated hydrogen gas, introducing CO2 into the reactor and allowing the CO2 to react with the in situ-generated hydrogen gas to form carbon monoxide, and allowing the carbon monoxide to contact the catalyst.
  • An advantage of the processes of the first and second aspects is that they reduce coking of the catalyst, which prolongs the catalyst lifetime. This is achieved by the carbon monoxide coordinating with the most acidic sites of the catalyst to inhibit formation of the coke precursors.
  • the process may further comprise adding a further weakly-coordinating compound to the reactor, wherein the weakly-coordinating compound is a compound that reduces the H-0 bond frequency of the aluminosilicate catalyst by about 1 to 300 cm-1 as measured by FT-IR.
  • the further weakly-coordinating compound may be selected from the group consisting of carbon monoxide, acetonitrile, dimethylsulfoxide, tetrahydrofuran, acetone, pyridine and tetrahydro thiophene. These are all commercially available organic compounds of relatively low cost which weakly coordinate to aluminosilicate catalysts and which may be included in the reactor to enhance the longevity of the catalyst.
  • the further weakly-coordinating compound is carbon monoxide.
  • the CO2 that is introduced into the reactor may be derived from a biological, combustion, or chemical transformation process.
  • An advantage of this feature of the process is that CO2 waste streams from biological sources (e.g. fermentation processes, such as processes for producing bioethanol from com), combustion processes (e.g. coal and gas fired power stations), or industrial processes (e.g. fertiliser or cement production) can be used as a feedstock in the process and converted into a value-added product.
  • biological sources e.g. fermentation processes, such as processes for producing bioethanol from com
  • combustion processes e.g. coal and gas fired power stations
  • industrial processes e.g. fertiliser or cement production
  • the oxygen-containing organic molecule may be derived from a fermentation process.
  • the fermentation process may be a process for producing a C1-C4 alcohol from a grain crop, such as corn.
  • An advantage of this feature is that it enables waste streams obtained from biological fermentation processes to be used as an inexpensive feedstock, reducing waste and generating a valuable product.
  • An example of a fermentation process is a fermentation process for producing short-chain alcohols, such as methanol and ethanol, from fermentation of grains and vegetables, such as sugar cane, molasses, corn, potato, barley, wheat or rye.
  • the C1-C4 alcohol may be ethanol.
  • ethanol e.g. corn ethanol
  • high value chemicals provides a commercially valuable alternative to its use as a fuel for combustion.
  • the fermentation process may be coupled directly or indirectly to the reactor used for the process of the first or second aspect.
  • An advantage associated with this feature is that it provides for cost reduction and improved efficiency in the overall process.
  • the oxygen-containing organic molecule may be introduced into the reactor in a feed stream having a water content of 30 volume% or more.
  • the water content may, in some embodiments, be 50 volume% or more, such as 80 volume% or more.
  • Waste streams obtained from biological fermentation processes typically have a high water content. Normally, feed streams having such high levels of water are unsuitable for use in processes using an aluminosilicate catalyst.
  • an advantage of the process described herein is that it is compatible with feed streams having a high water content without negatively affecting the aluminosilicate catalyst.
  • the process conditions ensure that the water is kept in the vapor phase during the process, eliminating the negative impacts on the catalyst, while simultaneously aiding in removing heavy hydrocarbon liquid deposits from the catalyst surface via vaporization.
  • the aluminosilicate of the catalyst may have a Si02:A103 ratio of between 20 and 50. Catalysts falling within this range experience minimal degradation when used in the process.
  • the catalyst may be a zeolite catalyst, preferably ZSM-5 or ZSM-11. Zeolite catalysts, and particularly ZSM-5 and ZSM-11, provide for optimal conversion of CO2 and H2 into the monocyclic aromatic compound. Alternatively, the catalyst may be a combination of a zeolite catalyst and a mixed metal oxide catalyst. [0019] The catalyst may be a metal-modified zeolite catalyst. The metal of the metal-modified zeolite catalyst may be selected from a group VIII, a group 11 or a group 12 metal. Modification of zeolite catalysts by metals in these groups enhances the catalyst activity, resulting in a higher product yield by comparison with non-metal-modified zeolite catalysts.
  • the oxygen-containing organic molecule is selected from C1-C4 alcohols, C1-C4 ethers, and combinations thereof.
  • the oxygen-containing organic molecule may be methanol, ethanol or combinations thereof, preferably ethanol.
  • the oxygencontaining organic molecule may be an ether, such as diethyl ether.
  • the monocyclic aromatic compound may be selected from the group consisting of benzene, toluene, xylene and combinations thereof.
  • Figure 1 is a graph depicting the beneficial effect of a carbon monoxide feed on extending catalyst lifetime.
  • Figure 2 is a table showing the total product composition of Example 1 and Example 3 at time on stream of 100 hours.
  • Figure 3 is a table showing product selectivity of Example 5. Ethanol conversion in these examples is 100%.
  • Figure 4 shows a schematic of an exemplary process for high-selectivity conversion of an oxygen-containing organic molecule to at least one monocyclic aromatic compound.
  • Figure 5 shows an embodiment of the process of Figure 4, including a regeneration process 300.
  • the monocyclic aromatic compounds described herein includes BTX (benzene, toluene, and xylene isomers, and mixtures thereof).
  • the monocyclic aromatic compounds may include ethylbenzene, and the mixture may then be referred to as BTEX.
  • Xylene isomers may comprise o-xylene, m- xylene, p-xylene, or combinations thereof.
  • oxygen-containing organic molecule will be understood to mean an organic molecule having at least one oxygen atom, at least one carbon atom, and at least one hydrogen atom.
  • the oxygen-containing organic molecule will be an aliphatic hydrocarbon having from 1 to 4 carbon atoms and one or more oxygen atoms.
  • the oxygen-containing organic molecule may be selected from C1-C4 alcohols, C1-C4 ethers, or C1-C4 esters, and combinations thereof, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, or combinations thereof, preferably ethanol, or diethyl ether, methylpropyl ether, or combinations thereof, or methyl formate, ethyl formate, methyl acetate, ethyl acetate, methyl propionate, or combinations thereof.
  • C1-C4 alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, or combinations thereof, preferably ethanol, or diethyl ether, methylpropyl ether, or combinations thereof, or methyl formate, ethyl formate, methyl acetate, ethyl acetate, methyl propionate, or combinations thereof.
  • the term “catalyst” refers to a dehydroaromatization catalyst utilized for the conversion of oxygen-containing organic molecules into monocyclic aromatic compounds.
  • the catalyst is a porous aluminosilicate or zeolitic material with a portion of its pores in the micro-, meso- and/or macro-range.
  • the catalyst may be a zeolite catalyst having a pentasil structure.
  • the zeolite catalyst may be ZSM-5 or ZSM-11.
  • the catalyst may be a combination of a zeolite catalyst and a mixed metal oxide catalyst.
  • bifunctional or tandem catalysts having a combination of a zeolite catalyst and a mixed metal oxide catalyst, have been reported in the literature (for example, in Nezam, Iman, Zhou, Wei, Gusmao, Gabriel S., Realff, Matthew J., Wang, Ye, Medford, Andrew J., and Jones, Christopher W. Direct aromatization of CO2 via combined CO2 hydrogenation and zeolite-based acid catalysis, Journal of CO2 Utilization, Volume 45, 2021, 101405, ISSN 2212-9820), wherein the metal oxides contain the active phase for carbon monoxide and hydrogen activation, and zeolites provide the active sites for C-C coupling.
  • These bifunctional catalysts represent an example of engineering alternate reaction pathways.
  • the zeolite catalyst may be a metal-modified zeolite catalyst.
  • the metal of the metal- modified zeolite catalyst may be selected from a group VIII, a group 11 or a group 12 metal.
  • the Si02:A103 ratio of the zeolite may vary between 20 and 50.
  • Zeolites such as ZSM-5 may be capable of converting oxygen-containing organic molecules into monocyclic aromatic compounds such as BTX via a complex sequence of oligomerization, isomerization, cracking and cyclization reactions that are believed to initiate on Bronsted acid sites of the zeolite.
  • the catalyst may be promoted or unpromoted. Promoting a catalyst is known in the art, and also referred to as loading.
  • the catalyst may be a heterogeneous catalyst comprising aluminosilicate in the range between about 1% to about 99% and preferably 75-99% with an amorphous silica or amorphous alumina, or a combination thereof, in a range of about 0% to about 99% and preferably 1-25%.
  • the aluminosilicate may contain at least 10% and preferably greater than 20% of its total porosity having a mean pore diameter of less than 20 nm.
  • the catalyst may have a total surface area of at least 90 m2/gram and preferably between 90-250 m2/gram.
  • the catalyst may be subject to a regeneration process, wherein the regeneration process comprises the introduction of inert gas and/or an oxidant and/or a reductive fluid at elevated temperature into the reactor.
  • the “weakly-coordinating compound” reduces the H-0 bond frequency of the zeolite catalyst or aluminosilicate catalyst framework by about 1 to 300 cm-1 as measured by FT-IR.
  • the weakly-coordinating compound may be a Lewis base.
  • the weakly- coordinating compound may be a labile compound.
  • Non-limiting examples of weakly- coordinating compounds include carbon monoxide, acetonitrile, dimethylsulfoxide, tetrahydrofuran, acetone, pyridine or tetrahydro thiophene.
  • the CO2 and H2 react in a reverse water gas shift reaction to produce carbon monoxide and water.
  • the carbon monoxide is a weakly-coordinating compound which can help to prolong the catalyst lifespan.
  • the carbon monoxide can also be converted into additional monocyclic aromatic compounds to increase the yield of the process.
  • the present disclosure provides a process for manufacturing at least one monocyclic aromatic compound, wherein the process comprises contacting an aluminosilicate catalyst with an oxygen-containing organic molecule in a reactor to produce the monocyclic aromatic compound and in situ-generated hydrogen gas. Three moles of hydrogen gas are generated per mole of monocyclic aromatic compound in the dehydroaromatization reaction of the oxygen containing organic molecule.
  • the process further comprises introducing CO2 into the reactor and allowing the CO2 to react with the in situ-generated hydrogen gas to form additional monocyclic aromatic compound.
  • At least a portion of the CO2 and in situ-generated hydrogen gas react in a reverse water gas shift process to form carbon monoxide and water. At least a portion of the carbon monoxide may be converted to the additional monocyclic aromatic compound.
  • the present disclosure also provides a process for manufacturing at least one monocyclic aromatic compound in which the process comprises contacting an aluminosilicate catalyst with an oxygen-containing organic molecule in a reactor to produce the monocyclic aromatic compound and hydrogen gas, introducing CO2 into the reactor, allowing the CO2 to react with the in situ-generated hydrogen gas to form carbon monoxide, and allowing the carbon monoxide to contact the catalyst.
  • the process may further comprise adding a further weakly-coordinating compound to the reactor.
  • the further weakly-coordinating compound may be selected from the group consisting of carbon monoxide, acetonitrile, dimethylsulfoxide, tetrahydrofuran, acetone, pyridine and tetrahydro thiophene.
  • the carbon monoxide produced in the reverse water gas shift process, and/or added to the reactor may be present in the reactor in an amount ranging from 0.1% by weight to 25% by weight, for example, in an amount ranging from 0.1% by weight to 10% by weight, or in an amount ranging from 3% by weight to 7% by weight, based on the overall weight of the components in the reactor.
  • the carbon monoxide may, for example, be present in an amount ranging from 5% by weight to 7% by weight.
  • the carbon monoxide may prolong the cycle time of the catalyst by about 15%.
  • the CO2 introduced into the reactor may be at least 50%, 60%, 70%, 80%, 90%, 95%, 97%, 98%, 99%, 99.9% or 100% pure.
  • the CO2 may be diluted with atmospheric air before or during introduction into the reactor. Alternatively, undiluted CO2 may be used.
  • the temperatures in the reactor may be within a range of from about 300 °C to about 700 °C, from about 350 °C to about 600 °C, or from about 400 °C to about 500 °C.
  • the temperature may be above 425 °C, above 450 °C, above 475 °C, and/or in a range of from about 450 °C to about 500 °C.
  • the pressure within the reactor may be within a range of from about 50 psi to about 500 psi, from about 75 psi to about 250 psi, from about 90 to about 150 psi, from about 100 psi to about 150 psi, or from about 100 psi to about 125 psi.
  • the reaction conditions may include a weight hourly space velocity (WHSV) of from about 0.01 to 10/hour, from about 0.1 to about 5/hour, from about 0.2 to about 2/hour, or from about 0.5 to about 1/hour.
  • the WHSV is defined as the weight of feed flowing per unit weight of the catalyst per hour.
  • Reactor pressure impacts conversion due to the Langmuir Adsorption Isotherm (LAI).
  • the LAI states that the adsorption of a molecule on a catalyst surface is proportional to the pressure/temperature. As such, as temperature increases, adsorption decreases and to overcome this, pressure must increase. Thus, to increase conversion yield of monocyclic aromatic compound per converted oxygen-containing molecule, the pressure within the reactor must be increased. However, this increase results in lower cycle times of the catalyst in the reactor. Accordingly, the present application provides an improvement by adding a weakly coordinating base to the reaction so that the cycle time of the catalyst increases.
  • the CO2 used in the processes of the invention may be derived from a biological, combustion, or chemical transformation process.
  • the CO2 may be obtained from biological sources (such as fermentation processes), combustion processes (such as coal and gas fired power stations), or industrial processes (such as fertilizer or cement production facilities).
  • the oxygen-containing organic molecule may be derived from a fermentation process.
  • the fermentation process may be a process for producing a C1-C4 alcohol (e.g. methanol, ethanol, etc) by fermentation of grains and vegetables, such as sugar cane, molasses, corn, potato, barley, wheat and rye.
  • a C1-C4 alcohol e.g. methanol, ethanol, etc
  • the CO2 and oxygen-containing organic molecule are derived from the same fermentation process and coupled, either directly or indirectly, with the reactor to provide the input streams for the processes of the invention.
  • the CO2 may be captured, compressed, and then introduced into the reactor.
  • CO2 obtained from alcohol production which is typically pure (>99.9%), can be relatively easily compressed and injected into the reactor.
  • the output streams of fermentation processes have a high water content. While feedstocks having a high water content are normally detrimental to catalytic processes involving zeolite catalysts, the processes of the present disclosure are capable of converting feed streams of alcohols with high water contents into the monocyclic aromatic products without substantial detriment to the catalyst. Therefore, the oxygen-containing organic molecule may be introduced into the reactor in a feed stream having a water content of 30 volume% or more, 50 volume% or more, or 80 volume% or more. It has been surprisingly found by the present inventors that increased water contents in the feedstocks are capable of leading to higher yields of monocyclic aromatic products in the processes of the invention. This is contrary to expectations based on the prior art, since higher water contents would be expected to de-aluminate zeolite catalysts, with consequential deleterious effects on both catalyst life and product yield.
  • Figure 4 depicts an exemplary schematic 100 for the high- selectivity conversion of an oxygen-containing organic molecule to a monocyclic aromatic compound.
  • a gas feed containing the oxygen-containing organic molecule enters the process as stream 102 and may include a stream from a fermentation process, which may comprise Cl- C4 alcohols.
  • Stream 102 may be obtained directly or indirectly from a fermentation process.
  • Stream 102 may be sent through exchangers and heaters 104 prior to reaction.
  • an additive stream 110 Prior to entry to a reactor 108, an additive stream 110 introduces a weakly -coordinating compound or precursor thereof to stream 102 prior to reaction resulting in a combined stream 112 that is input into reactor 108.
  • the reactor 108 is a fixed bed, fluidized bed, or moving bed.
  • the reactor 108 is a catalytic reactor, a gasifier, or a pyrolysis reactor.
  • the combined stream 112 may be heated by a fired heater 114 prior to entry into reactor 108 resulting in a hot feed 116.
  • the hot gas feed 116 enters reactor 108 and is reacted over the catalyst 118 bed(s) containing a dehydroaromatization catalyst.
  • the stream of weakly -coordinating compound or precursor thereof introduced via additive stream 110 reduces the H-0 bond frequency of the catalyst 118 (e.g., a zeolite or aluminosilicate framework) by about 1 to 300 cm-1 as measured by FT-IR.
  • the resulting product stream is output from the reactor 108 as output stream 120 and is cooled using cooler 122. Cooler 122 is optional.
  • the output stream 120, containing two-phase liquid and vapor products are separated in vessel 124.
  • the resulting products exit as a separated product stream 126.
  • the additive stream 110 may be introduced at any point prior to entry of the hot gas feed 116 into the reactor 108.
  • the additive stream 110 may be introduced to stream 102 after stream 102 is heated by fired heater 114.
  • the additive stream 110 may be introduced directly to the reactor 108 as a separate stream to the hot feed 116.
  • reactor 108 during conversion of the oxygen-containing organic molecule to the monocyclic aromatic compound, is subjected to a temperature of > 450°C, >500°C, and/or >550°C, in an outlet or inlet of reactor 108, or intra-reactor.
  • reactor 108 during conversion of a first composition comprising the oxygen-containing organic molecule to the monocyclic aromatic compound, is subjected to a pressure of 50 psi to about 500 psi.
  • the high- selectivity conversion of the oxygen-containing organic molecule to the monocyclic aromatic compound achieved via the process shown in schematic 100 is >25%, >45%, >65%, >75%, >85%, >95%, preferably >65%.
  • FIG. 5 shows an embodiment of the process of Figure 1, including a catalyst regeneration process 300.
  • the catalyst 118 is subject to a regeneration process, wherein said regeneration process comprises the introduction of regeneration compound 302 and operating the reactor 108 at a regeneration temperature.
  • the regeneration compound 302 is one or more of an inert gas, an oxidant, a reductive fluid, and any combination thereof.
  • operating the reactor 108 at a regeneration temperature includes gradually increasing the temperature in the reactor 108 to >450°C over a regeneration period.
  • the temperature of reactor 108 during the regeneration process is increased to between 300 °C and 700 °C, preferably from 400 to 550oC, or from 450 to 500oC during the course of the regeneration process.
  • the temperature is increased to about 500°C.
  • the oxidant is provided at low concentrations (e.g., about 1% oxygen gas in nitrogen gas) and increased over the course of the regeneration process.
  • Example 1 was repeated by replacing nitrogen with 10 mole % carbon monoxide in nitrogen. The reaction was stopped after 170 hours, a 13% life extension, when ethylene conversion was observed to drop below 90%.
  • Figure 1 shows ethylene conversion versus time on stream comparison of Example 1 and Example 2 and shows that addition of carbon monoxide resulted in a 20 hour ethylene conversion extension, thereby highlighting the beneficial effect that a weakly coordinating compound has on extending the catalyst life.
  • Example 1 was repeated by replacing nitrogen with 10 mole % carbon dioxide in nitrogen.
  • the entire reaction product was analyzed on-line using an Agilent 7890B GC equipped with a 100 meter DHA boiling point column and FID to monitor ethylene conversion and product selectivity.
  • Figure 2 shows the total product composition of Example 1 versus Example 3 at time on stream of 100 hours.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

L'invention concerne un procédé de fabrication d'un composé aromatique monocyclique. Le procédé consiste à mettre en contact un catalyseur d'aluminosilicate avec une molécule organique contenant de l'oxygène dans un réacteur pour produire le composé aromatique monocyclique et le gaz hydrogène généré in situ, et introduire le CO2 dans le réacteur et permettre au CO2 de réagir avec le gaz hydrogène généré in situ pour former un composé aromatique monocyclique supplémentaire.
PCT/IB2022/060127 2021-11-13 2022-10-21 Procédé de fabrication d'un composé aromatique monocyclique WO2023084343A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120036889A1 (en) * 2010-08-10 2012-02-16 Iaccino Larry L Methane Conversion Process
US8962902B2 (en) 2011-11-23 2015-02-24 Virent, Inc. Dehydrogenation of alkanols to increase yield of aromatics
US9388092B2 (en) 2011-12-20 2016-07-12 Saudi Basic Industries Corporation Performance of Ga- and Zn-exchanged ZSM-5 zeolite catalyst for conversion of oxygenates to aromatics
WO2018007485A1 (fr) * 2016-07-08 2018-01-11 Haldor Topsøe A/S Conversion de méthanol en aromatiques à base de gaz naturel
US20200308081A1 (en) * 2015-12-04 2020-10-01 Sabic Global Technologies B.V. Route for aromatic production from isopropanol and carbon dioxide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120036889A1 (en) * 2010-08-10 2012-02-16 Iaccino Larry L Methane Conversion Process
US8962902B2 (en) 2011-11-23 2015-02-24 Virent, Inc. Dehydrogenation of alkanols to increase yield of aromatics
US9388092B2 (en) 2011-12-20 2016-07-12 Saudi Basic Industries Corporation Performance of Ga- and Zn-exchanged ZSM-5 zeolite catalyst for conversion of oxygenates to aromatics
US20200308081A1 (en) * 2015-12-04 2020-10-01 Sabic Global Technologies B.V. Route for aromatic production from isopropanol and carbon dioxide
WO2018007485A1 (fr) * 2016-07-08 2018-01-11 Haldor Topsøe A/S Conversion de méthanol en aromatiques à base de gaz naturel

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
NEZAM IMAN ET AL: "Direct aromatization of CO2via combined CO2hydrogenation and zeolite-based acid catalysis", JOURNAL OF CO2 UTILIZATION, ELSEVIER, NL, vol. 45, 20 January 2021 (2021-01-20), pages 1 - 21, XP002807845, ISSN: 2212-9820, DOI: 10.1016/J.JCOU.2020.101405 *
NEZAM, IMANZHOU, WEIGUSMAO, GABRIEL S.REALFF, MATTHEW J.WANG, YEMEDFORD, ANDREW J.JONES, CHRISTOPHER W: "Direct aromatization of CO2 via combined CO2 hydrogenation and zeolite-based acid catalysis", JOURNAL OF CO2 UTILIZATION, vol. 45, 2021, pages 101405

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